反应详情

温度

120 °C

In a sealable, flask a mixture of 1-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (0.150 g, 0.321 mmol) in 1,4-dioxane (5 mL) was prepared. (3-(tributylstannyl)-1H-pyrazol-5-yl)methanol (0.137 g, 0.353 mmol) was added followed by tetrakis(triphenylphosphine)palladium (0) (0.150 g, 0.130 mmol). The mixture was flushed with N2, and flask was sealed. The mixture was then heated to 120° C. for 14 h. After cooling to rt, the mixture was diluted with DMF, and filtered through a plug of celite to remove any solids. The liquid was concentrated under reduced pressure, and the residue was dissolved in DMF. The DMF solution was purified by prep HPLC to give 0.037 g of an off-white solid as the 1-(7-(5-(hydroxymethyl)-1H-pyrazol-3-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione. LCMS: m/e 529.2 (M+H)+, ret time 1.78 min (method 2). 1H NMR (500 MHz, MeOD) δ ppm 8.65 (s, 1 H) 7.98 (s, 1 H) 7.56-7.80 (m, 5 H) 7.16 (s, 1 H) 4.81 (s, 2 H) 4.15 (s, 3 H) 3.83-3.87 (m, 2 H) 3.63-3.68 (m, 2 H) 3.40-3.44 (m, 2 H) 3.34-3.39 (m, 2 H).

1. customwas prepared
2. customThe mixture was flushed with N2, and flask
3. customwas sealed
4. temperatureAfter cooling to rt
5. additionthe mixture was diluted with DMF
6. filtrationfiltered through a plug of celite
7. customto remove any solids
8. concentrationThe liquid was concentrated under reduced pressure
9. dissolutionthe residue was dissolved in DMF
10. customThe DMF solution was purified by prep HPLC